Chapter 5 245 a.m. Was A Choice
August
I’m still at the office like it’s a damn Airbnb I forgot to check out of. Elbows deep in paperwork, eyes glazed, posture shot to hell. Basically, a corporate gargoyle with Wi-Fi.
Outside my window, the sky’s bleeding from blue to bruised purple. I barely clock it. I’m too busy drowning in contracts and redlines, letting the legalese sandblast my brain.
A knock cuts through the silence.
“It’s by the door,” I mutter, not looking up.
“You’re still here?” Kelley’s voice slides in, full of judgment and expensive cologne. “I texted you hours ago.”
That gets my attention. I blink up. There he is: tie gone, top buttons open, jacket slung over his shoulder like he just walked out of a campaign shoot instead of my office.
All angles, lashes, and the kind of natural I don't give a fuck energy that lets him walk out of a brutal work week looking ready to go break hearts in the street.
“You did not,” I say, reaching for my phone. One swipe later: six missed texts, three emails, a group chat I definitely should’ve muted.
“Exhibit A.” He flashes his screen with a smug grin.
I sigh and set my phone down. “My bad. I was neck-deep in this contract for legal. Got tunnel vision.”
“Bro, it’s Friday. Past seven. The only people who should be working right now are ER doctors and nightclub staff. You’re neither.” He drops into the chair opposite me like he owns it.
“I just want to get this out tonight.”
“You’re the CEO, August. Who exactly is gonna fire you?” he deadpans. “Because if it’s you, I want that in writing. I’ll frame it and hang it over your mom’s fireplace.”
I lean back, stretch. My spine snarls in protest. “Stuff needs to get done.”
“And it will. Monday.” He studies me, charm edged with something older. “You’ve been living in this building, man. I miss my friend, not this corporate gargoyle you’re cosplaying.”
That lands harder than I want it to.
He claps his hands once. Decision made. “Alright. One drink. We’ll talk shop for twenty minutes so you don’t combust, then I’ll distract you with poor life choices.”
I huff out a laugh. “One drink. But I pick the spot. I’m not going anywhere the floor’s stickier than a toddler’s fingers.”
“Relax. I’m not taking the future James dynasty to a biohazard.” He’s already on his feet. “We’ll go somewhere with linen napkins and a view. You can expense it or I’ll put it on Mom’s tab. Either way, it’s handled.”
A few more hours wouldn’t fix the contract anyway. I shove my tablet into my bag and grab my jacket. He holds the door open.
“Come on, Mr. Chicago.” His arm hooks around my shoulders like we’re nineteen again. “Let’s get mildly irresponsible.”
An hour and one drink in, I remember exactly why nights with Kelley should come with a waiver.
We’re at one of his “hidden gems,” a rooftop you only reach by walking through a busted industrial building that looks like a front for money laundering.
Outside? Total dump. Rusted loading docks.
Flickering security lights. A door that sticks like it hasn’t been opened since the Clinton administration.
Inside?
Straight skyline porn.
Leather booths. Low house music humming through hidden speakers. Strings of amber lights draped across the ceiling like somebody tried to bottle sunset. Lake Michigan glittering beyond the railing like someone spilled diamonds across the horizon.
A breeze rolls through the open space, warm and heavy with June humidity and the faint smell of lake water.
The bartender daps Kelley up the second we sit.
“Wilde. Same tab as last time?”
“You know it,” Kelley says, handing over a black card without even glancing at the menu. “Whatever my boy wants, keep it coming.”
I order a beer.
He orders something top-shelf for me anyway.
Around us the rooftop buzzes—glasses clinking, laughter rising over the music, somebody arguing about the Cubs at the bar. A woman in a red dress snaps photos by the railing while her friends shout directions like amateur directors.
Kelley studies me over the rim of his glass.
“You realize people assume you’re the responsible one.”
“I am.”
He laughs. “No. You just look responsible. Big difference.”
“What’s that supposed to mean?”
“It means you wear a suit and talk like you’re about to close a merger even when you’re ordering tacos.”
“That’s called being articulate.”
“That’s called terrifying the waiter.”
I lean back. “And you?”
“Oh, I lean into low expectations,” he says easily. “It’s liberating.”
“Low expectations,” I repeat.
“People think I’m just here for the vibes.” He shrugs. “Meanwhile I’m buying half the room.”
I shake my head. “You’re unbelievable.”
“And yet,” he says, lifting his glass with a grin, “I’m still your favorite.”
“Reluctantly. Don’t let Monroe hear that.”
“I’ve got a decade on him.”
“Oh, is my poor Kelley jealous?” I mock, pitching my voice into the whiny tone of a petulant child.
Kelley chuckles. “Jealous of Monroe? Nah. I just knew you before the facial hair and the Armani suits.”
“I love you too, brother,” I tease.
“That’s not what I said,” Kelley replies smoothly.
Kelley lifts his glass again like he’s just delivered the final word on the subject.
A burst of laughter erupts from the bar behind us. Someone drops a glass. The DJ nudges the music louder, bass rolling softly under the conversation.
That’s Kelley.
Twelve years of friendship and he still manages to dodge anything remotely sentimental with the grace of a politician in an election year.
I let it go.
Because if there’s one thing I’ve learned about Kelley Wilde, it’s that the man will show up for you a thousand different ways, he just refuses to say it out loud.
“You still messing with April?” I ask eventually, knocking back another sip. The beer’s cold and clean, but it doesn’t quiet the itch to check my phone again. I flip it over. Screen lights up: nothing.
Kelley squints like he’s scrolling his mental Rolodex labeled Questionable Decisions. “April… April…” Snap. “Nah, that’s Amy on Thursday. April got cut.”
“Lemme guess. She breathed too loud?”
“She fell asleep after sex, man,” he says, scandalized. “Then had the audacity to ask for breakfast. Like I didn’t make it clear: no sleepovers, no coffee, no getting emotionally attached.”
“So have sex at their place.”
He recoils. “Hell no. You know how delicate my back is. Plus, last time I tried that? Veronica.”
We both wince. No further explanation needed.
I laugh, low and bitter. “Right. Veronica’s baby daddy and his little sidekick, Mr. Glock.”
Kelley shudders, shaking off the memory. “Yeah, I like my drama in box scores and quarterly reports now. My place has a doorman, security, and a hard ‘get-the-fuck-out-by-8’ policy. Peace is priceless.”
“Preach.” We clink. This time it feels more like ritual than celebration.
My fingers drift back to my phone. Flip. Check. Still nothing.
Kelley clocks it instantly.
“What’s that about?” he asks, waving down the bartender for another round.
“What’s what?”
He just lifts a brow. “You’ve checked that phone more than the market checks the Fed. You good?”
I rub the back of my neck. “Yeah. Nothing serious.”
“Uh-huh. It’s supposed to be a night out. I haven’t seen you in weeks—even though we share office space—and you’re over there married to your notifications.”
I slide my phone face-down. “Was just checking the time.”
“It’s 10:30, grandpa. We’d barely be done pre-gaming in college. So what’s really going on?”
“We’re not in college anymore,” I deflect.
“Which is why you’re lying like a man with something to hide.” He narrows his eyes. “Come on. Who we blackmailing?”
As if on cue, my smartwatch buzzes against my wrist. Kelley grins. “Fourteen,” he says.
“I didn’t even check it.”
“You looked.”
I sigh. “It’s not work, if that’s what you’re thinking.”
“Then who?”
“Mom and Carver want me to go to some fundraiser next month. PR appearance for his reelection campaign.”
Kelley sneers. “Why would anyone reelect that prick?”
“No clue.” I knock back another swallow. “But if people knew half the truth—”
“You could tell her,” he says quietly. “Your mom.”
“Tell her what?” My laugh comes out rough. “She won’t believe it. And even if she did, it’d wreck her. She’s the only parent I’ve got left.” I shrug, swallowing around the lump. “Easier to carry it than hand it off.”
He nods. Doesn’t push. That’s the thing about him: he’ll poke until the moment it matters, then back off like it’s second nature.
A waitress appears. Blonde, black mini dress, smile sharpened to a weapon. “Another round, gentlemen?”
Before I can answer, Kelley straightens like he heard his cue. Grin dialed to lethal.
Here we go.
By the time Katherine’s blushing and giggling in his booth, I’ve surrendered my seat, my beer, and my patience.
“You two make a beautiful couple,” I tell her on my way out. “Just make sure you stretch first.”
A shiver runs through her.
And it has nothing to do with the AC.
I relocate to the far side of the bar, giving him room to be whoever he needs to be tonight. From here, I can still see them: his hand on her knee, that shampoo-commercial hair toss, her laugh floating across the room, light and easy.
Same Kelley. Different girl. There’s no jealousy, not really. I’ve had more than my share of nights. It’s something quieter. Emptier. Like I’ve wandered off the edge of my own life.
I take a long pull of beer, let the bitterness sit.
That’s when she drops into the stool beside me like she owns the air.
Red hair. Killer legs. Rumpled blazer and pencil skirt like she lost a fight with a long day.
The bar is humming—ice rattling in shakers, a burst of laughter from a group at the high-tops, the low buzz of conversation riding over a bluesy guitar track drifting from the speakers. Neon beer signs glow against exposed brick, washing everything in a soft electric haze.
“Vodka cranberry, please,” she says, voice frayed at the edges.
The bartender nods. She slaps a black Amex on the bar like it owes her money.
“Rough day?” I ask.